Tetrahydrofuran → HCID 14496321, compound

HRID 327867Notes

Reaction equation

HRID 327867 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].O1CCCC1.[BH4-].[Na+]>CO>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:9][CH:8]=2)=[CH:11][CH:12]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 14512984HCID 14512984, compound

Product 1

HCID 14496321HCID 14496321, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

120.9 g (0.4 mol) of 4'-acetyl-4-benzyloxybiphenyl, 400 ml of tetrahydrofuran and 100 ml of methanol were supplied into a four-necked flask equipped with a stirrer and a thermometer. Then 15.14 g (0.4 mol) of sodium borohydride was added at 15°-25° C. over a period of 2 hours. The mixture was kept at the same temperature for 5 hours, then poured into ice-water and extracted twice with 500 ml of chloroform. The organic layer was concentrated under reduced pressure to obtain 117.4 g of 4-benzyloxy-4'-(1-hydroxyethyl)biphenyl in a 96.5% yield.

Workup

  1. customequipped with a stirrer
  2. extractionextracted twice with 500 ml of chloroform
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-523a8279df704d92938dc521852c536c
Source dataset
uspto-grants-1993_12
Patent number
US05274168

Reaction notes

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